Aspidospermine

Details

• Internal ID: c38061d2-3f43-40d7-8993-a8e82804d14a
• Taxonomy: Alkaloids and derivatives > Aspidospermatan-type alkaloids
• IUPAC Name: 1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5-trien-8-yl]ethanone
• SMILES (Canonical): CCC12CCCN3C1C4(CC3)C(CC2)N(C5=C4C=CC=C5OC)C(=O)C
• SMILES (Isomeric): CC[C@]12CCCN3[C@H]1[C@@]4(CC3)[C@@H](CC2)N(C5=C4C=CC=C5OC)C(=O)C
• InChI: InChI=1S/C22H30N2O2/c1-4-21-10-6-13-23-14-12-22(20(21)23)16-7-5-8-17(26-3)19(16)24(15(2)25)18(22)9-11-21/h5,7-8,18,20H,4,6,9-14H2,1-3H3/t18-,20-,21-,22-/m1/s1
• InChI Key: ARQOGCYMPUOVHK-ZHHKINOHSA-N
• Popularity: 143 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀N₂O₂
• Molecular Weight: 354.50 g/mol
• Exact Mass: 354.230728204 g/mol
• Topological Polar Surface Area (TPSA): 32.80 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.73
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Aspidospermin
• (-)-Aspidospermine
• 466-49-9
• 1-Acetyl-17-methoxyaspidospermidine
• CHEMBL519457
• CHEBI:28463
• NSC61811
• NSC-19508
• NSC-61811
• U1475W62Q5
• Aspidospermidine, 1-acetyl-17-methoxy-
• Vincaminorine
• WLN: T C6 B5665 2AB S BX IN QN JH&&TTTJ GO1 IV1 M2
• UNII-U1475W62Q5
• EINECS 207-376-7
• NSC 19508
• BRN 0048882
• ASPIDOSPERMINE [MI]
• TimTec1_000915
• 5-23-12-00210 (Beilstein Handbook Reference)
• SCHEMBL918176
• Vincaminorein (Aspidospermine)
• DTXSID70196883
• 1-[ethyl(methoxy)[?]yl]ethanone
• HMS1536J13
• NSC19508
• BDBM50252054
• CCG-35302
• CCG-36039
• NCGC00174986-01
• NCI60_005440
• 1-Acetyl-17-methoxyaspidospermidine, 9CI
• 1-(17-methoxyaspidospermidin-1-yl)ethanone
• 1-(17-Methoxyaspidospermidin-1-yl)-ethanone
• C09042
• BRD-K06579228-001-01-6
• Q27103707
• ETHANONE, 1-(17-METHOXYASPIDOSPERMIDIN-1-YL)-
• 1-((3aR,5aR,10bR,12bR)-3a-Ethyl-7-methoxy-2,3,3a,5,5a,11,12,12b-octahydro-1H,4H-6,12a-diaza-indeno[7,1-cd]fluoren-6-yl)-ethanone
• 1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5-trien-8-yl]ethan-1-one
• 1935-07-5
• 2H-3,7-Methanoazacycloundecino(5,4-b)indole-9-carboxylic acid, 7-ethyl-1,4,5,6,7,8,9,10-octahydro-10-methyl-, methyl ester, (7S-(7R*,9R*))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9842	98.42%
Caco-2	+	0.8566	85.66%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6343	63.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9310	93.10%
OATP1B3 inhibitior	+	0.9482	94.82%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.6482	64.82%
P-glycoprotein inhibitior	-	0.4883	48.83%
P-glycoprotein substrate	+	0.7441	74.41%
CYP3A4 substrate	+	0.6277	62.77%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	+	0.4404	44.04%
CYP3A4 inhibition	+	0.7838	78.38%
CYP2C9 inhibition	-	0.9168	91.68%
CYP2C19 inhibition	-	0.6561	65.61%
CYP2D6 inhibition	+	0.5604	56.04%
CYP1A2 inhibition	-	0.7400	74.00%
CYP2C8 inhibition	-	0.6253	62.53%
CYP inhibitory promiscuity	-	0.5430	54.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6883	68.83%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9901	99.01%
Skin irritation	-	0.8249	82.49%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8931	89.31%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.5474	54.74%
skin sensitisation	-	0.8582	85.82%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7410	74.10%
Acute Oral Toxicity (c)	III	0.5892	58.92%
Estrogen receptor binding	+	0.6448	64.48%
Androgen receptor binding	+	0.6788	67.88%
Thyroid receptor binding	+	0.5758	57.58%
Glucocorticoid receptor binding	+	0.6217	62.17%
Aromatase binding	-	0.5737	57.37%
PPAR gamma	+	0.5678	56.78%
Honey bee toxicity	-	0.9124	91.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.7607	76.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.45%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.34%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.01%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.14%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.94%	91.11%
CHEMBL3474	P14555	Phospholipase A2 group IIA	88.97%	94.05%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.30%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.20%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.05%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.90%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.07%	97.14%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.69%	95.17%
CHEMBL5028	O14672	ADAM10	83.79%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.05%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.95%	92.62%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.61%	93.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.36%	94.00%

Plants that contains it

• Aspidosperma pachypterum
• Aspidosperma polyneuron
• Aspidosperma pyrifolium
• Aspidosperma quebracho-blanco
• Geissospermum argenteum
• Strempeliopsis strempelioides
• Strychnos angolensis
• Tabernaemontana divaricata
• Vallesia glabra
• Vinca minor

Cross-Links

• PubChem: 227613
• LOTUS: LTS0028800
• wikiData: Q27103707